Preparation of p-(benzylamino) benzenesulphonamides



Patented Mar. 22, 1938 UNITED "STATE S PATENT OFFICE ranimwrrou or P-(BENZYLAMINO) nnuzmsunrnommnus Paul Emile 'Charles Goissedet and Robert Ludovic Dcspois, Choisy Le Roi, France, assignors to Societe des Usines Chemiques Rhone- Pouienc, Paris, France No Drawing. Application July-2, 1936, Serial No. 88,592. In Great Britain February 18,

Claims.

The present invention relates to the preparation of a new group of aromatic compounds.

The object of the invention is the preparation of new compounds of valuable bactericidal properties.

The compounds forming the subject of the present invention are derivatives of p-aminobenzenesulphamide, substituted in the amino group by an aralkyl group. The compounds may by causing the aralkyl halides (which may be fund the filtrate evaporated to dryness. The res- 1 substituted in the nucleus or not) to react on paminobenzenesulphamide, or by causing p-aminobenzenesulphamide to condense with an aromatic aldehyde and then hydrogenating the resulting Schifi's' base in the presence of a suitable catalyst.

The following examples illustrate how the invention maybe carried out in practice, but it is to beunderstood that the-invention isin no way limited to the details given in these examples:

' Example 1 130 grams of p-benzylidine aminobenmnesulphamide are dissolved in 1300 cc. of dioxane and hydrogenated at 50 C. in the presence of active nickel. When the absorption of hydrogen is finished the catalyst is separated by filtration idue is recrystallized from alcohol.

p-Benzylaminobenzenesulphamide'is thus obtained in a nearly theoretical yield in .the form of almost colourless crystals melting at 175 C.

Example 2 34.4 grams of p-aminobenzenesulphamide are a dissolved in 500 cc. of boiling water, 20 grams of calcium carbonate, and 12.7 grams of benzyl chloride, 'are added and the mixture heated to boiling with stirring for 3 hours. The product is acidified by hydrochloric acid and the p-benzylaminobenzenesulphamide which is precipitated is separated by filtration." Est/recrystallization .from acetone the same product as thatobtained in Example 1 is obtained in almost theoretical yield.

,' benzyl halide Example 3 r 10 grams of p-(o-hydroxybenzylidine-aminol-- benzenesulphamide are dissolved in 200 cc. of dioxane and hydrogenated at ordinary temperature in the presence of active platinum; after absorption of the theoretical quantity of hydrogen the catalyst is separated by filtration and the filtrate is evaporated. The residue is recrystallized from 50% alcohol; p-(o-hydroxybenzylamino)benzenesulphamide is obtained in very good yield in the form of white needles melting at "183? C.

Example 4 13.8 grams of p-(p-hydroxybenzylidine-amirfo) benzenesulphamide are dissolved in 300 cc. of dloxane and hydrogenated in the presence of active nickel at ordinary temperature. After absorption of the theoretical quantity of hydrogen, the catalyst is separated. by filtration, the filtrate is evaporated to dryness and the residue is recrystallized from acetone.

p- (p-Hydroxybenzylamino) benzenesuiphamide is thus obtained in almost theoretical yield in the form of colourless crystals melting at 206 C.

' Example 5 20.8 grams of the sodium salt of benzaldehydem-sulphonic acid and 20.85 grams oifv the hydrochloride of p-amino benzenesulphamide are dissolved in 500 cc. of water. This solution is hydrogenated at ordinary temperature in the presence of platinum. After filtering 01! from the catalyst there is obtained by-evaporation of the solutionthe sodium salt of p-(m-sulphobenzyl amino) benzenesulphamlde.

What we claim is:-

1. The new bactericidal compounds of the general formula: 0

where X represents a member of the group corisisting of H, OH, and SOaH:

'2.; The new'bactericidalacompound p-benzylaminobenzenesulphamide.

,3. The new bactericidal compound p-(o-hydroxylbenzylamino) benzenesulphamide.

4. The new bactericidal compound the sodium salt of p-(m-sulphobenzylamino)benzenesulphamid. a

5. .41- process for the preparation of new aromatic compounds consisting in causing a to react with p-aminobenzenesul- 'phamide.

ROBERT LunovIc pusrors.

PAUL EMILE CHARLES GOISSEDET. d 

